Azo dyestuffs and process of preparing them



Patented 05515, 1929 UNITED STATES PATENT OFFICE HERMANN WAGNER, OF BADSODEN-ON-TAUN US, AND ERICH FISCHER OF HOCHST-ON- MAIN, GERMANY,ASSIGNORS T0 GENERAL ANILINE WORKS, INC., OF NEW YORK,

N. 'Y.,-A CORPORATION OF DELAWARE AZO DYESTUFFS AND PROCESS OF PREPARINGTHEM No Drawing. Application filed July 19, 1927, Serial Nb. 207,016,and in Germany July 29, 1926.

The present invention relates to the new azo dyestuffs of the generalformula:

wherein R represents an aromatic residue of the group including thebenzene and naphthalene series, X stands for hydrogen, alkyl, aryl, oraralkyl and wherein the aromatic nuclei may be further substituted.

These dyestuffs are obtainable for instance by coupling a diazo compoundof the benzene or naphthalene series with a compound of the generalformula:

wherein X represents hydrogen, alkyl, aryl,

or aralkyl, and wherein the naphthalene nucleus may be furthersubstituted. They ing formula:

' ice is added an excess of a sodium carbonate form red powders whichdye wool even yel-' lowish-red to bluish-red-tintsof good fastness tolight.

The -followir'ig examples serve to illustrate our invention withoutlimiting it thereto, the parts being by weight.

1. 333 parts ofthe product of the follow- NaOaS obtainable by the actionof chloroformic-acidethylester upon sodium2-amino-8-hydroxynaphtha]ene-G-sulfonate, are dissolved in water. To thesolution which is cooled'with der and corresponds most probably to thefollowing formula:

0 H II o-oonn NaOsS O t OH NH. OCzHs Naois some obtainable by the actionof chloro-formicacid-ethylester upon sodium-1-amino-8-hy-.droxynaphthalene-3.6-disulfonate, are coupled in the manner indicated inExample 1 with a diazo solution prepared from 421 parts ofmeta-xlyidine. The dyestuff which separates forms, when filtered bysuction and dried, a red powder dyeing wool a very even, bluish-red tintof good fastness to light and corresponding most probably to the formulaThe aminonaphthol derivatives and diazo compounds used for thepreparation of the dyestuffs may be of the most varied kind. Thus theremay be used as coupling components for instance the following compounds:J

The reaction products of chloroeformicacid-ester uponQ-ethylamino-S-hydroxynaphthalene-G-sulfonic acid,2-amino-8-hydroxynaphth'alene or the like. The new products canadvantageously be used in the manufacture of diazoand polyazo-dyestuffs.

When using as diazo component orthoaminophenols, ortho-aminonaphthols"or derivatives of these compounds, the dyestuffs thus obtainable can beafterchromed in known manner.

We claim: Y

1. As new products the azo dyestuffs of the general formula wherein Rrepresents an aromatic residue of the group including the benzene andnaphthalene series, X stands for hydrogen, alkyl,

aryl, or aralkyl, and wherein the aromatic nuclei may be furthersubstituted, being red powders and dyeing wool even yellowish-red tobluish-red tints of good fastness to light.

2. As new products the azo dyestufls ofthe following formula: l

Y1 on 2 X1 N=N NadgS wherein X stands for CH or N(CH ).CO.CH Y for H oralkyl, one Z for H and the other Z for NH.CO.CO H and V for H or SO Na,

being red powders which dye wool very even 0 yellowish-red to bluish-redtints of good fastness to light. I

1 3. As new products'the azo dyestufl's of the following formula :V

NaO=S wherein X stands for CH or .iron 00.011

group and Y for H or CH being red powders which dye wool very evenyellowishred tobluish-red tints of good fastness to light.

4. As a new product the azo dyestufl' of the following formula:

. l v O being a. red powder which dyes wool very even yellowish-redtints of good fastness to light.

In testimony whereof, we aflix our signatures.

7 HERMANN WAGNER.

ERICH F ISCHER

